The best chances

At 135lb
Duran -Late stoppage win for Duran
Arguello- Whitaker wins a close decision
Mosley- Mosley was at his best at Lightweight, can Sweet Pea withstand the power?

At 140lb
Pryor- It is almost hard to imagine the frustration Pryor would have trying to catch him?
Tszyu- He had ring smarts, was experienced and handled southpaws better than most, i think he lands one?
Mayweather - I just don't see Whitaker beating him?

Whitaker is an all time great, certainly a top 3 Lightweight of all time, it gets more difficult for him as he moves up in weight.

Can you imagine Whitaker V Loche?

Would Salvador Sanchez have made it to Lightweight by the late 80's had he lived? They almost certainly would've met sometime 1987-88 as Sanchez wouldn't have turned 30 until 1989.